Discotic octasubstituted tetrapyrazinotetraazaporphyrazines

Abstract

Octasubstituted tetraphyrazinotetraazaporphrazine and compositions forming an electron acceptable discotic liquid crystal phase are disclosed. Said compounds and the metal complexes are easily soluble in an organic solvent such as chloroform or dichloromethane etc and are insoluble in acetone and alcohols; and therefore a columnar phase by silica gel/dichloromethane, recrystallization from tetra-hydrofuran or refining through solid liquid extraction by acetone is possible. Furthermore, stability in a giant molecular can be expected and a functional membrane can be formed by a solution cast method etc., thereby employing as an electon or photoelectron material or an indication element.

What is claimed is: 
     
       1. A discotic liquid crystal phase having electron-accepting character and comprising a tetrapyrazinotetraazaporphyrazine compound of the following formulas (1a) or (1b): ##STR5## wherein R is selected from at least one of C 6  H 13 , C 7  H 15 , C 8  H 17 , C 9  H 19 ,C 10  H 21 ,C 11  H 23  and C 12  H 25  and M is Cu, Zn, Pb, Fe, Co or Ni. 
     
     
       2. The discotic liquid crystal phase of claim 1 wherein R is C 6  H 13 . 
     
     
       3. The discotic liquid crystal phase of claim 1 wherein R is C 7  H 15 . 
     
     
       4. The discotic liquid crystal phase of claim 1 wherein R is C 8  H 17 . 
     
     
       5. The discotic liquid crystal phase of claim 1 wherein R is C 9  H 19 . 
     
     
       6. The discotic liquid crystal phase of claim 1 wherein R is C 10  H 21 . 
     
     
       7. The discotic liquid crystal phase of claim 1 wherein R is C 11  H 23 . 
     
     
       8. The discotic liquid crystal phase of claim 1 wherein R is C 12  H 25 . 
     
     
       9. The discotic liquid crystal phase of claim 1 wherein M is Cu. 
     
     
       10. The discotic liquid crystal phase of claim 1 wherein M is Zn. 
     
     
       11. The discotic liquid crystal phase of claim 1 wherein M is Pb. 
     
     
       12. The discotic liquid crystal phase of claim 1 wherein M is Fe. 
     
     
       13. The discotic liquid crystal phase of claim 1 wherein M is Co. 
     
     
       14. The discotic liquid crystal phase of claim 1 wherein M is Ni.